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Compare 145 Vacation Homes in Kailua with updated reviews, rates, and availability.

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (366)
"Great location and the place had everything we needed for our family. Could use some updates and fixes, but a good price for Hana. We appreciated the beach gear and the kids didn't want to leave."
The price is AED 716
AED 1,465 total
includes taxes & fees
4 May - 5 May
Fisher's Hana Bay Hale, Across from Hana Bay

STHA-2017/0002 Across from Hana Bay

9.6 out of 10, Exceptional, (365)
"Nice place. PM, Kathy is very nice"
The price is AED 639
AED 1,308 total
includes taxes & fees
12 May - 13 May
STHA-2017/0002 Across from Hana Bay

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (195)
"A perfect area and a perfect stay! The hosts think of everything and even include some nice touches like banana bread and chocolates. The property is immaculate and the condo is extremely comfortable. We would recommend this property to anyone."
Kaiholo Hale

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

10.0 out of 10, Exceptional, (215)
"I have stayed in many rental homes and this is by far the best equipped rental home I have ever stayed in. We love to cook and usually can’t find enough pots and pans and utensils and this house had them all.We also had the privilege of their neighbors having goats and baby goats and cows which we enjoyed seeing from the deck of the house The house was also close enough to major towns And easy to find I would definitely stay here again on our next trip to Maui "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

9.8 out of 10, Exceptional, (220)
"Cozy, clean, & comfortable. "
The price is AED 1,194
AED 2,413 total
includes taxes & fees
23 Apr - 24 Apr
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

9.6 out of 10, Exceptional, (97)
"Loved the pool and beach, great location, comfortable and clean. Perfect. "
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

Beautiful Home in paradise!

9.6 out of 10, Exceptional, (164)
"Wanted a place for my family to stay while we enjoyed the road to Hana in Maui. This place checked the boxes. "
Beautiful Home in paradise!

Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

10.0 out of 10, Exceptional, (118)
"The accommodations were outstanding. My entire family came over with kids and grandparents age 10 to 86 and everyone had a place. My parents stayed in the Ohana, which was absolutely fantastic. The rest of the house had enough king size beds for myself and my daughters and their husbands. The kids split amongst the two other bedrooms. The game set up upstairs couldn’t have been better. The kitchen function so well. Our favorite spot was evening dinners out on the deck. Highly highly recommend...
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

Mountain to Ocean Views Pole House @ Maui Adventure Villa

9.8 out of 10, Exceptional, (216)
"We had a splendid time. The “Treehouse” was truly above the tree line and the view was breathtakingly beautiful. The owner, John, was friendly and very helpful. We hope to return soon."
Mountain to Ocean Views Pole House @ Maui Adventure Villa

Waterfall House - Private House Overlooking the Ocean!

9.8 out of 10, Exceptional, (24)
"Pros: Incredible setting and the grounds are beautiful. Whale watching from the hot tub was probably the highlight of our trip. The pool gets the perfect amount of sun on the nice days. The whole property is very calm and relaxing. The people onsite are incredibly friendly and do not disturb the guests.Cons:The circle bed in the listing photos in incredibly uncomfortable. Getting in and out you or rolling or kneeling on marble to get on a mattress that has seen better decades. We would've slept...
Waterfall House - Private House Overlooking the Ocean!

Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

9.8 out of 10, Exceptional, (196)
"Our family of 6 adults and four children ages 6, 10, 10 & 12 enjoyed this little piece of paradise. Plenty of pool towels and lounge chairs. The outdoor patio furniture was great with shade for those wanting to stay out of the sun. The pool was an instant hit and the yard is huge! Dining outdoors was a nice option with the large dining table and lots of chairs. There is a gas grill, 2 fridges and enough room to park 4-5 cars. There is a large capacity washer and dryer and the outside shower...
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

Luxury Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (38)
"We had a great time. Location is beautiful. House is comfortable, clean, and well-equipped. The view is amazing. Pool and whirlpool were a hit. Close to stores/restaurants in Makawao. Good hiking nearby. The hosts were responsive and helpful. Really can’t say enough about the views. I spent more time enjoying the views than reading my book! Didn’t even think about turning on the TV!"
Luxury Upcountry Villa with breathtaking views

OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

9.8 out of 10, Exceptional, (7)
"We could not be more grateful for our experience in this home. Steps from our lawn was a beautiful beach with unforgettable sunsets on the beach or the fully open air lanai. The home was perfectly and newly appointed, spotless, and comfortable. The management team facilitated an easy check in and also checked in while we were there. Thank you! We’ll be bac!"
OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

North Shore Ocean View Cottage

10.0 out of 10, Exceptional, (136)
"We love this property! Our standards are high when it comes to cleanliness and updated finishes/fixtures and linens. It’s quiet and private. Brigitte and Dave are great and were extremely welcoming and helpful with questions or recommendations for our Maui stay. Many properties just don’t match what this cottage has to offer. Quality is top notch in our view. Second visit and we would stay again in a heartbeat. Thanks Dave and Brigitte!!"
North Shore Ocean View Cottage

Kula Luxury Retreat With Stunning Ocean & Mountain Views!

10.0 out of 10, Exceptional, (70)
"KeoKea ranch is beautiful. The hosts are super responsive and very nice. If you like quiet and incredible views and some four leggeds to entertain you, just do it!"
Kula Luxury Retreat With Stunning Ocean & Mountain Views!

Sugar Beach Resort condo with ocean view, AC - surf, bike & golf

8.8 out of 10, Excellent, (49)
"All good, except the screen doors need to be fixed."
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf

Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

9.6 out of 10, Exceptional, (106)
"Nice property with plenty of space, great location on the island, super communicative and polite host, and such a great backyard/outdoor area. Would highly recommend!"
The price is AED 1,084
AED 3,879 total
includes taxes & fees
19 Apr - 20 Apr
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

Historic Upcountry Maui Property With Pool, 5 Bedrooms, Sleeps 16

10.0 out of 10, Exceptional, (61)
"16 of us stayed at this beautiful property. Two Families, 12 children total. We have nothing bad to say. All of our expectations were met. The listing is true and accurate. Communication with the property manager was always prompt and efficient.We would definitely stay her again."
The price is AED 5,124
AED 10,132 total
includes taxes & fees
19 Apr - 20 Apr
Historic Upcountry Maui Property With Pool, 5 Bedrooms, Sleeps 16

BEACHFRONT MAUI KIHEI HOUSE

9.8 out of 10, Exceptional, (157)
"The property is beautiful. We had a family gathering of kids and grandkids. The space fit our family’s needs well. There is a large grass area between the house and beach. You can play volleyball, bags, and croquet. The beach was a minute walk from the house. The Maui sunsets were spectacular. Not a good swimming beach but a wonderful beach for exploring and watching the sea turtles come out and rest on the rocky sand. "
BEACHFRONT MAUI KIHEI HOUSE

Stunning Beach Front Townhouse

10.0 out of 10, Exceptional, (90)
"Firstly, Susan was so wonderful to deal with- thank you for being so welcoming and accommodating- we really appreciated the late checkout- with a 3 year old toddler with us…he was able to nap and that made such a wonderful difference to our last day in paradise. The view is amazing! Would love to stay there again someday soon. "
Stunning Beach Front Townhouse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Kailua

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1050)
"Had a gift bag waiting for us! Easy pool and beach access"
Sugar Beach Resort

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (422)
"Pros: Beautiful view, well maintained property, great location with access to activities and restaurants while right on a fairly quiet beach, kitchen was well equipped for a rental, Wi-fi worked well Cons: The construction noise while we were there was intermittently insanely load, the beds are small, the pool is full sunrise to sunset "
Maui Sunset

Maui Schooner Resort

3.5 star property
9.2 out of 10, Wonderful, (450)
"We liked everything there. Beautiful place!"
Maui Schooner Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.